theMilesWeKeep
Me? Flexible? Not Really. Unless It Involves International Flights… or Occasionally Yoga
April 20, 2026
What started as a simple escape to Bali (with a casual “maybe Thailand?” tossed in) has officially turned into our most ambitious trip yet. Somewhere between flight searches, flexibility, and a little bit of chaos, we’ve built an itinerary that spans five countries: Beijing, Singapore, Bali, Thailand, and Tokyo.
And honestly? We didn’t force it. We let the trip become what it wanted to be.
When Life Forces a Better Plan
Here’s the twist we didn’t see coming: a rotator cuff surgery.
Never did I think my best friend’s shoulder would end up saving us from some serious travel headaches, but here we are. Originally, we had planned a long layover through Abu Dhabi in the United Arab Emirates. With everything going on globally, that routing started to feel… less than ideal.
Because we were intentionally holding off on booking flights to see how she’d recover (two weeks post-op and only five weeks before departure), we had the flexibility to pivot.
As a travel advisor, I’ll be honest: this is not the textbook approach. Waiting that long to book international flights can backfire. But in this case, it gave us optionality. And with some very intentional flight tracking, we landed on a route that felt better, safer, and somehow… more exciting.
(P.S. We will have to reverse this picture on the upcoming adventure!)
How Bali Turned Into Five Countries
People keep asking: how did this expand so much?
Short answer: flexibility.
Longer answer: we let the flights lead.
Instead of locking ourselves into a rigid plan, we stayed open. When great routes popped up, we followed them. That’s how a Bali trip evolved into stops in:
- Beijing
- Singapore
- Bali
- Thailand
- Tokyo
This style of planning definitely isn’t for everyone. It requires a tolerance for uncertainty and a willingness to adapt. But for us, it’s consistently led to some of our best travel experiences.
Our Planning Timeline (What Actually Worked)
We didn’t just wing it. There was structure—just with room to breathe.
8–10 weeks out
We started with the basics:
“Must-do’s,” “nice-to-do’s,” and the underrated category: “not needed.” This helped us stay grounded as the trip expanded.
6–8 weeks out
This is where things got real:
Visas, entry requirements, common travel mishaps, and learning a few key phrases in each language. (A simple hello and thank you goes a long way.)
5 weeks out
Big milestone:
We booked our major international flights. This is later than we’d typically recommend, but it worked in our favor this time.
4 weeks out
Now we started shaping the experience:
Hotels, excursions, and figuring out how long we actually needed in each place.
3 weeks out
Logistics mode:
Internal flights. And let me tell you, this trip has more of them than anything we’ve done before.
2 weeks out
Final prep begins:
Packing lists, last-minute add-ons, and coordinating with the bank for local currency. Oh, and daily phone calls of excitement…
1 week out
Information overload (in the best way):
Thousands of social media posts, saved reels, and shared tips for each destination.
Week of
The controlled chaos:
Packing, final confirmations… and yes, securing an international driving permit at the absolute last minute.
(10/10 would not recommend cutting it that close.)
The Biggest Takeaway
This trip is shaping up to be our greatest adventure yet. Not because it’s the most packed or the most ambitious, but because we stayed open.
Open to change.
Open to better routes.
Open to the unexpected.
Sometimes the best travel plans aren’t the most perfectly organized; they’re the ones that evolve.
And if this is just the planning phase… we can’t wait to share what the trip itself brings. Stay tuned this week as we embark on our most epic trip yet.
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